4.8 Article

Synthetic Strategy for Construction of Highly Congested Tetracyclic Core (6-5-7-4) of Harziane Diterpenoids

Journal

ORGANIC LETTERS
Volume 23, Issue 11, Pages 4088-4093

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c00769

Keywords

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Funding

  1. National Key Research and Development Program o f China [2018YFC0310905]
  2. National Science Foundation of China [21632002, 21871012]
  3. Guangdong Natural Science Foundation [2010B03030700002]
  4. Shenzhen Basic Research Program [2019SHIBS0004]

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The structurally intriguing tetracyclic core of complex harziane diterpenoid was successfully constructed in 14 steps from commercially available compound. Key methods used include Mn/Cu-mediated oxidative 1,3-dicarbonyl radical cascade cyclization reaction and Au-catalyzed diastereoselective formal [2 + 2] cycloaddition.
The structurally intriguing tetracyclic core of complex harziane diterpenoid was constructed in 14 steps from commercially available 3-ethoxycyclohex-2-en-1-one. The key steps were a Mn/Cu-mediated oxidative 1,3-dicarbonyl radical cascade cyclization reaction, which diastereoselectively formed the core of dimethylbicyclo[3.2.1]octane structure, and a Au-catalyzed diastereoselective formal [2 + 2] cycloaddition for construction of the harziane diterpenoid tetracyclic framework. The developed method paves the way for achieving total synthesis of this type of complex natural product.

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